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| Names | |
|---|---|
| IUPAC name 15-cis-7,8,11,12,7′,8′,11′,12′-Octahydro-ψ,ψ-carotene | |
| Systematic IUPAC name (6E,10E,14E,16Z,18E,22E,26E)-2,6,10,14,19,23,27,31-Octamethyldotriaconta-2,6,10,14,16,18,22,26,30-nonaene | |
| Other names 15-cis-Phytoene | |
| Identifiers | |
3D model (JSmol) | |
| ChEBI | |
| ChemSpider |
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| KEGG |
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| UNII | |
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| Properties | |
| C40H64 | |
| Molar mass | 544.952 g·mol−1 |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Phytoene (/ˈfaɪtoʊiːn/) is a 40-carbon intermediate in the biosynthesis ofcarotenoids.[1] The synthesis of phytoene is the firstcommitted step in the synthesis of carotenoids inplants. Phytoene is produced from two molecules ofgeranylgeranyl pyrophosphate (GGPP) by the action of the enzymephytoene synthase.[2] The two GGPP molecules are condensed together followed by removal of diphosphate and proton shift leading to the formation of phytoene.
Dietary phytoene andphytofluene are found in a number of human tissues including the liver, lung, breast, prostate, colon, and skin.[3] Accumulation of these carotenoids in the skin may protect the skin by several mechanisms: acting asUV absorbers, asantioxidants, and as anti-inflammatory agents.[4][5]
Phytoene is a symmetric molecule containing threeconjugated double bonds. Phytoene has a UV-Vis absorption spectrumtypical for a triply conjugated system with its main absorption maximum in theUVB range at 286 nm and withε1% of 915.[clarification needed][citation needed]
Analysis of several fruits and vegetables showed that phytoene andphytofluene are found in majority of fruits and vegetables.[6] In contrast to all other carotenoids, phytoene and phytofluene, the first carotenoid precursors in the biosynthetic pathway of other carotenoids, absorb light in the UV range.
The structure of phytoene was established and proven by total synthesis, by theBasil Weedon group in 1966.[7]
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